ammonia; lithium in tetrahydrofuran T=-30°C; 0.666667 h;

1: 32percent AcOOH/AcOH, NaHCO3 / CH2Cl2 / 1.5 h 2: aq. KIO4, p-TsOH / acetone / Ambient temperature 3: 1.) t-BuOK / 1.) THF, 1.5 h, 2.) THF, from -5 to 0 deg C, 1.5 h 4: H2, HCl/MeOH / 5percent Pd/C / 2585.7 Torr 5: 81 percent / aq. KMnO4, AcOH / acetone / Ambient temperature View Scheme